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1,3‐dipolar cycloaddition of diazomethane to azolopyridazines. The synthesis of isomeric 7‐methyl‐7 h ‐ and 8‐methyl‐8 h ‐pyrazolo[4,3‐ d ]azolopyridazmes
Author(s) -
Merslavič Marjo,
Petrič Andrej,
Rozman Damjana,
Stanovnik Branko,
Tišler Miha
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260234
Subject(s) - diazomethane , chemistry , cycloaddition , chlorine atom , 1,3 dipolar cycloaddition , chlorine , medicinal chemistry , tricyclic , nucleophilic substitution , nucleophile , stereochemistry , ring (chemistry) , organic chemistry , catalysis
1,3‐Dipolar cycloaddition of diazomethane to 6‐chloro substituted azolopyridazines 1‐4 produces isomeric pairs of 7‐methyl‐7 H ‐ 9‐12 and 8‐methyl‐8 H ‐pyrazolo[4,3‐ d ]azolopyridazines 13‐16 . The nucleophilic substitution of chlorine at position 6 affords the corresponding 6‐amino 17, 20, 23, 26, 29,32,35 and 38 , 6‐methoxy 18, 21, 24, 27, 30,33, 36 , and 39 and 6‐hydrazino derivatives 19, 22, 25, 28, 31, 34, 37 , and 40 of these tricyclic systems.